Abstract

-Sultams are the sulfonyl analogues of-lactams, and 3-oxo- -sultams are both-lactams and -sultams and, therefore,susceptible to nucleophilic attack at eitherthe acyl or the sulfonyl center. They arenovel inactivators of serine enzymes. Thesecond-order rate constant for theinactivation of elastase at pH 6 by N-benzyl-4,4-dimethyl-3-oxo- -sultam is 768 M-1 s-1, which is 103-fold greater than However, in contrast to N-acyl -sultams, which sulfonylate the active site serine residue to form a sulfonate ester, 3acylation followed by slow deacylation to regenerate the active enzyme.